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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winona holiday rentals

Deluxe Apartment, 2 Bedrooms, Kitchen | Mountain view

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (243 reviews)
"The room and resort was great! The staff was excellent and sweet! We will definitely be back!"
United States
Stacey
The price is 3.468.336 ₫
3.763.145 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Cold Spring Plymouth Resort
House (3 Bedrooms) | Interior

2. Walk to Beach! Family Lake Winnipesaukee Home

Walk to Beach! Family Lake Winnipesaukee Home
3.0 star property
Moultonborough
The price is 3.045.000 ₫
12.014.363 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Walk to Beach! Family Lake Winnipesaukee Home
Classic Apartment, Non Smoking | Private kitchen | Full-sized fridge, microwave, oven, stovetop

3. 9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
10.0 out of 10, Exceptional, (1 review)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is 7.901.250 ₫
11.518.762 ₫ total
includes taxes & fees
23 Aug - 24 Aug
9 Lake Street
House (1 Bedroom) | Interior

4. 6 Mi to Polar Caves! All-season Getaway w/ Sauna

6 Mi to Polar Caves! All-season Getaway w/ Sauna
3.0 star property
Plymouth
The price is 7.153.965 ₫
9.849.149 ₫ total
includes taxes & fees
10 Aug - 11 Aug
6 Mi to Polar Caves! All-season Getaway w/ Sauna
Apartment (1 Bedroom) | Interior

5. Lake Getaway: Walk Across Street to Private Beach!

Lake Getaway: Walk Across Street to Private Beach!
3.0 star property
Gilford
6.0 out of 10, (1 review)
The price is 3.780.000 ₫
6.853.613 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Lake Getaway: Walk Across Street to Private Beach!
House (2 Bedrooms) | Interior

6. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (1 review)
"We’ll kept "
United States
Denise
The price is 5.555.460 ₫
12.114.572 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Cozy Tuftonboro Escape: Steps to Private Beaches!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winona Hotel Reviews

Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

8/10 Good
"Very friendly staff, clean rooms great location"
Nikki 2-night trip
Posted 2 hours ago
Fireside Inn & Suites Gilford

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Winona?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winona stay.

What’s there to see and do in Winona?

Explore the area and family-friendly sights such as Squam Lakes Natural Science Center, or get out into nature at a spot like Winona Lake. In the wider area, you’ll find Lake Winnipesaukee and Lake Waukewan.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals provide amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.